San Francisco - Experience Designer and Coach, Founder of Trail Mavens
Sasha believes in learning by doing. Since she can remember, she’s always wholeheartedly poured herself into every situation, in order to give and glean as much as she can. She’s also a natural encourager, giving others confidence or hope in moments of fatigue, doubt or fear, and instinctive facilitator of community. Almost a year ago, Sasha launched Trail Mavens, an outdoor adventure and community-building company created for women and women only. She’ll design, organize and produce epic adventures where extraordinary women teach, learn, build and explore alongside one another throughout California’s expansive and inspiring wilderness. After each conversation I had with Sasha about her Somewhere, I left with more energy than I had going in; and wishing I could take part in a future Trail Mavens trip. Alas, men are not allowed. I love her for that! Throughout Sasha’s interview there’s a lot to take away, but how Sasha approaches a challenge is both practical and profound, and worth highlighting: Respect the magnitude of what’s ahead, put your whole heart into it, but focus on what’s in front of you, make tiny steps towards large gains.
- Let’s get there.
TSP: Can you please share a little bit about your past? Where you’ve been? What you’ve done?
SC: My path, at least until more recently, has been pretty straightforward. I was an energetic high school student who worked hard and loved life, and then an energetic college student that worked hard and was involved in everything. Post-college, I worked as an admission officer at my alma mater, and then stayed on another year to get an MA in Education. After that, I taught elementary school in East Palo Alto, and eventually left to take a job designing and facilitating games with the Go Game.
While reflecting on the past isn’t something I tend to spend too much time doing (I focus my energy more on the present and future) it’s funny to see how patterns emerge when you look back. When people describe me, they always mention ‘enthusiasm’ and ‘energy.’ On my high school cross country team, you’d find me cheering like a madwoman on the side of a course for all my teammates running races after my own. In college, I spent most of my time on stage, in musicals and improv shows, engaging crowds, tour guiding, teaching, and planning large-scale events. In every job I’ve ever had, I’ve tried to put my peers first and totally pour myself into the experience. Why not, right?
The real link between all my jobs, though, has been about reaching out with all my energy and inviting people into an experience, whether it’s a lighthearted, adventurous, cultural, story-rich, or a completely brand-new-kind-of-scary experience or challenge they didn’t think they’d be able to face.
TSP: “Until more recently”, what does that mean?
SC: For five years, the Go Game was the perfect job for me, and then both my parents passed away in the space of a year and a half, and being that enthusiastic person on stage began to require more of me than I had to give, so I created my own brand-new-kind-of-scary experience. I left my friends, brother, and home and traveled the world for ten months. I’ve always been a big traveler and feel good rolling with the punches, but the day-in, day-out of not knowing what would come next was like flexibility boot camp.
While traveling one morning in mid-April 2013, on the South American leg of my adventure, I was cooking breakfast over my camp stove in a tiny Andean village. The sun rose over the mountains and warmed my face as I stirred oats and apples together in my tiny pot, and in that moment, I was struck with an enormous sense of fulfillment and well-being: I both had and knew everything I needed. I wanted to share the moment with my two best girl friends back in SF, and realized how odd it was that I had never combined the outdoors - my favorite thing - with my favorite people. In fact, I didn’t even know what they knew about the outdoors, because it never came up in conversation. I became determined to go backpacking with them as soon as I got back home. About two seconds later, it occurred to me that I shouldn’t stop there. That elusive feeling of groundedness and confidence was something I’d love to share with all women. About an hour of brainstorming later, I came up with a name: Trail Mavens.
It’s amazing what happens when you take the blinders off, and you just get out there. If you’d asked me two years ago if I’d start a business, my answer would have been along the lines of, “No sir. No chance.” However, somewhere along the path of “Flexibility Boot Camp” the line between what I could and couldn’t do blurred.
TSP: What courage and strength, Sasha. Would you share how you approach such large trials and challenges?
SC: There are two parts to this answer. When presented with a major challenge, I try not to think about its magnitude. Instead, I respond to the moment in front of me, and figure out what needs to happen right now. Focusing on each moment allows me to act without getting overwhelmed by the size of my goal. I get this from my background in improv, which trains you to keep your eyes and ears open and to be supremely present. The success of the larger theatrical performance is contingent upon the success of each moment. When you focus on what’s in front of you, you’re able to assess, appreciate and act, ultimately producing one applause-worthy moment at a time.
The other part comes from running. With running, you need to move forward, you need to persevere. I’ve had to learn to be comfortable with discomfort. When I go the track and do a speed workout, my legs feel like they’re on fire. It’s a matter of acknowledging the pain, becoming familiar with it, embracing it and moving forward. Just because I feel tired doesn’t mean I can’t get up and go run. A feeling should not inhibit an action. It can guide an action, but should in no way stop an action.
TSP: What are you up to now?
SC: I returned to SF in November 2013, and I launched Trail Mavens, a company dedicated to bringing awesome groups of women together to collaborate, connect, and have a fantastic time, while teaching and learning hard outdoors skills. My role is to facilitate that experience for groups of women by eliminating the barriers that keep us from them, both in a very practical sense (I provide transportation, gear, food, campsites, etc.) and in a group-dynamics sense.
TSP: Can you tell us a little more about Trail Mavens?
SC: Of course. To start, there are two important omissions from our Trail Mavens outings: technology and men. Without the Internet to distract us, it’s so much easier and more fulfilling to connect with the people around you. In all-female groups, interpersonal connectivity is much richer. There’s no weird competitive vibes around being the first to the top, quickest tent architect or best fire-builder. (Sorry guys, it happens.)
The outdoors and the skill building are important, but ultimately they’re the larger agent for creating a deep-seated sense of “I’ve got this” that extends well past the trip’s end. Not by coincidence, that’s totally the story I’ve been living since I got back from my trip. Every day is like a Nike ad: I just do it. It’s sort of like the 20 Mile March: it doesn’t matter if you don’t feel prepared to take the leap, you breathe into your fear and do it anyway.
TSP: How many Trail Mavens adventures have you produced since starting the company?
SC: We’ve completed six to date and I have five more planned for the rest of this year. When colder weather and rain set in, we can start exploring snowshoeing to Sierra Club huts in Tahoe, and foraging for mushrooms in Big Sur.
TSP: Have you encountered any unique surprises or discoveries since embarking on this new mission?
SC: One big surprise is how every group immediately gels and meshes together so well. It’s been incredible to see how quickly people bond; and, how they continue to engage with one another after the trip. In the incubation phase of Trail Mavens, I had this idea of getting applicants and curating the trips based on the applications to ensure great connectivity, however, to my great delight, I found that to be completely unnecessary.
Another surprise has been to see how valuable the trip is to the Mavens – as well as to those who’ve only heard about the idea. Meaningfully engaging with nature without men around is unique and extremely important. I mean, how often does that actually happen? Very rarely, at best, is my guess. Which is unfortunate. The physical, mental and social growth and breakthroughs that occur on these trips is powerful.
TSP: What is one of the more unique elements of a Trail Mavens adventure?
SC: There’s always incredible conversation – it gets real, really fast. It’s often that Mavens talk about life things they don’t always get to talk about in their everyday context. Collecting a group of intelligence women from different backgrounds and social circles creates a unique setting to cut through the bullshit and get straight to the deep thoughts, big questions and general hilarity that comes with the freedom of the setting.
TSP: Where do you hope to go next, personally and professionally?
SC: In the most immediate sense, I’m excited to continue filling and leading more Trail Mavens adventures in California. I want to explore curating groups of women who share a passion or experience (working moms, tech pros, athletes, artists), and integrating my coaching practice with Trail Mavens to deepen the learning for trip participants.
While my current audience is primarily women between 23-35, these trips would be equally awesome for groups of mid-career women, retired women, or better yet, blended age groups. I’d love to find a partner to help offer Trail Mavens ‘scholarships’ to women for whom trip costs are prohibitive. In the largest sense, I want to build a thriving community of women who are in touch with their own Greatness, and (because of Trail Mavens) have a huge network of peers they can call on, both to go hiking in desolate wilderness areas or to chat about career moves, world politics, or motherhood.
As a woman who didn’t grow up in a ‘camping family’ and didn’t learn outdoors skills until adulthood, and then always from boyfriends, I want to disrupt the status quo where men (boyfriends, dads, husbands) are nearly always the outdoor ‘experts,’ teachers, and fire-starters. I want women to take on that role for their friends, daughters, sons, and husbands. I want women to be the fire-starters! It’s funny - it's hard to differentiate between the personal the professional on this question because one of the major benefits of leading Trail Mavens trips is the opportunity to build my own tribe of strong, passionate women in my life who are friends, confidants, and inspirations.
TSP: What about Trail Mavens, where do you hope to take it?
SC: Trail Mavens lies in an interesting grey zone between travel, the outdoors, women’s groups, do-it-yourself, book clubs, Iron Chef, dance parties, and coaching – It’s a big grey zone, as you can see. I’m exploring partnerships in and gaining inspiration from all those areas.
I’m also focusing on building the Trail Mavens community, and my goal is to get the word out to as many interested women as possible. The more trips that happen, the bigger and more valuable and vibrant the community is, the more Trail Mavens is able to have an impact. These trips provide me with feedback on what works best and also how best to facilitate and empower women in the outdoors context, which, in turn, provides me with more information on how to empower women broadly.
TSP: How can we, the TSP community, help you get to where you want to go?
SC: I'm very open to collaboration, so if you know female facilitators or skilled outdoorswomen who are interested in sharing their knowledge, please reach out! Whether you’re a naturalist, a pro kayaker, a rock climber, a nature photographer, or a yoga instructor, there’s someone on a trip you’ll inspire.
Are you a marketing or PR professional who resonates with this and would like to help tell the Trail Mavens story? Great! My experience is in teaching, coaching, and facilitation, so while leading trips is really comfortable for me, I’m sure my marketing and communication efforts could use some brush-ups.
And as I mentioned before, I want to expand the Trail Mavens community. Our next happy hour is September 18 in SF, and you’re all invited! Sign up for the Trail Mavens newsletter for all the details, and to hear about trips past and upcoming – You can sign up for our newsletter here. Finally, register for a trip to experience Trail Mavens in all its glory – You can register here. I’d be happy to offer a Somewhere Project discount for readers.
Sasha on Instagram